I think I agree with Beagle: The more I look at the Caps' situation this season, with all the injuries, the goalies settling into inconsistent mediocrity, and the age/injury/contract situation preventing any significant return for any "veteran presence" players they'd like to give up (are a few 5th round draft choices going to make any difference in the team's future?), the more it looks like basically standing pat is the way to go now.
I know Leonsis made a promise to Ovie to try to get him as many chances at a Cup as he could, but anyone can see that the Caps' chances of even making any significant noise in the playoffs are slim and none, and Slim is saddling his horse to ride out of town. Any moves they'd try to make to "strengthen" the team for a run now will simply drive them further into the age/salary cap box canyon they are already in now. The only problem is, standing pat doesn't do anything for the longer term competitive chances of the franchise.
The most useful thing that could happen for the long-term health of the franchise would be for Ovie to go to management and say "Look, earlier in my career I might have hoped for more championship success. But I can read the tea leaves of what's happening here. I'm satisfied with a legacy of one ring and a run at the career goal-scoring record. As long as you give me something to work with to keep scoring, do what you have to do to the roster for the longer-term benefit of the team."